A calm lake surrounded by dense forest and a cloudy sky.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Weston vacation homes

A swimming pool at night with blue lighting.

1. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is AED 331
AED 559 total
includes taxes & fees
18 Oct - 19 Oct
Business or Weekend escape
A campfire with a wooden table and benches by a lake.

2. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is AED 628
AED 1,281 total
includes taxes & fees
11 Oct - 12 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

3. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is AED 579
AED 1,194 total
includes taxes & fees
13 Oct - 14 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

4. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AED 790
AED 2,130 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

5. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
United States
Maxx V.
5BR Beach House, Water Views, Steps to Beach, Backyard
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

6. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is AED 1,447
AED 3,021 total
includes taxes & fees
21 Oct - 22 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A bedroom with two beds, a wooden dresser, and a mirror.

7. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is AED 1,131
AED 1,762 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 1-bedroom house in welcoming Bridgeport
A white room with a round table, two benches, and a window with a view of houses.

8. Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (29 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
Stay at Black Rock Harbor
Open concept kitchen

9. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (26 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
5BR Beach House, Game Room + Huge Backyard
A two-story house with a porch, stone steps, and a variety of plants.

10. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is AED 2,456
AED 4,836 total
includes taxes & fees
20 Oct - 21 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

11. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AED 3,823
AED 5,682 total
includes taxes & fees
11 Oct - 12 Oct
Beechmont - Perfect for Family Retreat!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

12. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AED 1,028
AED 2,606 total
includes taxes & fees
14 Oct - 15 Oct
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

13. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is AED 579
AED 976 total
includes taxes & fees
21 Oct - 22 Oct
Centric property close to all the great things in the city
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

14. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (19 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is AED 856
AED 2,214 total
includes taxes & fees
15 Oct - 16 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

15. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is AED 1,419
AED 2,997 total
includes taxes & fees
2 Nov - 3 Nov
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

16. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is AED 387
AED 1,200 total
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A multi-story house with a dock and boats, surrounded by dense forest.

17. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is AED 1,214
AED 4,514 total
includes taxes & fees
14 Oct - 15 Oct
North Cliff House - Private Dock & Sauna
A living room with a sofa set, a coffee table, and a television on a stand.

18. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is AED 1,124
AED 2,200 total
includes taxes & fees
14 Oct - 15 Oct
Spacious Stamford Home | Family, Work, Parking
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

19. Elite room stay

Elite room stay
Bridgeport
The price is AED 760
AED 1,256 total
includes taxes & fees
21 Oct - 22 Oct
Elite room stay
A modern living room with a white sofa, a glass coffee table, and a piano.

20. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is AED 1,275
AED 2,441 total
includes taxes & fees
28 Oct - 29 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Weston Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Great stay , easy valet parking, nice amenities ..will be back."
Paul 2-night trip
Posted 7 hours ago
Hyatt Regency Greenwich